Ethyl Acetate → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74187

反応式

HRID 74187 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[CH:24](OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:24]=[N:15][C:14]=2[CH:16]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

生成物 1

HCID 674977225-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole収率 31.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.20 g, 0.646 mmol), triethyl orthoformate (5 mL) was added a catalytic amount of p-toluenesulfonic acid monohydrate, and this was heated to 100° C. for 1.5 hours. The reaction mixture was cooled, ethyl acetate and water added, and this was extracted. This was washed with water, dried over magnesium sulfate, and after concentration the precipitated crystals were filtered off. These were washed with a hexane/ethyl acetate mixture solution, and dried to yield the title compound (65 mg, 31.5% yield) as light reddish-brown crystals.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionthis was extracted
  3. washThis was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationafter concentration the precipitated crystals
  6. filtrationwere filtered off
  7. washThese were washed with a hexane/ethyl acetate mixture solution
  8. customdried

出典と根拠

ORDレコード
ord-7fb7c65b3cb14bfebba4c88cb89f09ce
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

関連ノート

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